49791-77-7Relevant academic research and scientific papers
One-pot synthesis of benzene-fused medium-ring ketones: Gold catalysis-enabled enolate umpolung reactivity
Xu, Zhou,Chen, Hongyi,Wang, Zhixun,Ying, Anguo,Zhang, Liming
, p. 5515 - 5518 (2016)
Enolate umpolung reactivities offer valuable and potentially unique alternatives over the enolate counterparts for the construction of ubiquitous carbonyl compounds. We disclose here that N-alkenoxypyridinium salts, generated readily upon gold-catalyzed additions of protonated pyridine N-oxide to C-C triple bonds of unactivated terminal alkynes, display versatile enolate umpolung chemistry upon heating and react with tethered arene nucleophiles in an SN2′ manner. In a synthetically efficient one-pot, two-step process, this chemistry enables expedient preparation of valuable benzo-fused seven-/eight-membered cyclic ketones, including those of O-/Nheterocycles, from easily accessible aryl-substituted linear alkyne substrates. The reaction yields can be up to 87%.
Access to Indole-Fused Benzannulated Medium-Sized Rings through a Gold(I)-Catalyzed Cascade Cyclization of Azido-Alkynes
Greiner, Luca C.,Inuki, Shinsuke,Arichi, Norihito,Oishi, Shinya,Suzuki, Rikito,Iwai, Tomohiro,Sawamura, Masaya,Hashmi, A. Stephen K.,Ohno, Hiroaki
supporting information, p. 12992 - 12997 (2021/07/20)
Because benzannulated and indole-fused medium-sized rings are found in many bioactive compounds, combining these fragments might lead to unexplored areas of biologically relevant and uncovered chemical space. Herein is shown that α-imino gold carbene chem
A hierarchy of aryloxide deprotection by boron tribromide
Punna, Sreenivas,Meunier, Stephane,Finn
, p. 2777 - 2779 (2007/10/03)
Aryl propargyl ethers and esters are cleaved selectively in the presence of aryl methyl ethers and esters by boron tribromide in dichloromethane. Under the same conditions, allyl ethers undergo very rapid Claisen rearrangement, and benzyl ethers are also cleaved more rapidly than propargyl. A mechanism involving intramolecular delivery of bromide to the propargyl terminus is proposed.
